(3S,9R,9aS)-3-hydroxy-3,5,5,9-tetramethyl-1,3,5,6,7,8,9,9a-octahydro-2H-benzo[7]annulen-2-one | 1272548-43-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,9R,9aS)-3-hydroxy-3,5,5,9-tetramethyl-1,3,5,6,7,8,9,9a-octahydro-2H-benzo[7]annulen-2-one
• 英文别名: (3s,9r,9As)-3-hydroxy-3,5,5,9-tetramethyl-5,6,7,8,9,9a-hexahydro-1h-benzo[7]annulen-2(3h)-one；(3S,9R,9aS)-3-hydroxy-3,5,5,9-tetramethyl-1,6,7,8,9,9a-hexahydrobenzo[7]annulen-2-one
• CAS: 1272548-43-2
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: QAPAQJXDVXZJFN-ZETOZRRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (5R,5aS)-1,1,5,8-tetramethyl-1,2,3,4,5,5a,6-heptahydrobenzo[1,2-a][7]-annulene 、 (6R,7S)-2,2,6-trimethyl-10-methylenebicyclo[5.4.0]undec-1(11)-ene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (3S,9R,9aS)-3-hydroxy-3,5,5,9-tetramethyl-1,3,5,6,7,8,9,9a-octahydro-2H-benzo[7]annulen-2-one 、 (1S,2R)-2,2,6-trimethylbicyclo[5.4.0]undec-7-en-9-one
  参考文献：
  名称：

  Male-Specific Sesquiterpenes from Phyllotreta Flea Beetles

  摘要：

  Flea beetles in several genera are known to possess male-specific sesquiterpenes, at least some of Which serve as aggregation, pheromones that attract both sexes. In continuing, research on the Chemical ecology of Phyllotreta flea beetles, six new male specific sesquiterpenes were identified, one from P. striolata (hydroxyketone 9) and five from P. pusilla (aldehydes 10-12 and 14 and alcohol 13),, both species are crop pests. The minute amounts from beetles provided mass. spectra, and chromatographic data but were insufficient for complete structure determination. However, it was discovered that the new compounds could all be produced by applying organic reactions to previously identified flea, beetle sesquiterpenes, and the resulting, larger amounts of material permitted, definitive. structure analysis by NMR. Molecular Modeling was used in conjunction with NMR to define relative configurations of several newly created stereogenic centers. The absolute configurations of natural 9-14 were established by chiral gas chromatography/. mass spectrometry. In electrophysiologicial tests (GC-EAD) conducted with P. striolata compound 9, was detected with high, sensitivity by) the beetle;antennae, which is consistent with a pheromonal function.,The research opens new possibilities. for using behavioral Chemicals to monitor or Manage these pest species.

  DOI：

  10.1021/np100608p